# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_22
_database_code_depnum_ccdc_archive 'CCDC 1540876'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H40 O3 Si'
_chemical_formula_sum            'C21 H40 O3 Si'
_chemical_formula_weight         368.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.7593(3)
_cell_length_b                   6.7689(2)
_cell_length_c                   21.0839(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.6220(10)
_cell_angle_gamma                90
_cell_volume                     2176.24(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4338
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      67.43

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.065
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14953
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.334
_diffrn_reflns_theta_max         67.728
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3894
_reflns_number_gt                3248
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex2'
_computing_cell_refinement       'Buker SAINT'
_computing_data_reduction        'Buker SAINT'
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.6866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3894
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.64611(3) 0.07230(6) 0.66727(2) 0.03422(14) Uani 1 1 d . . . . .
O1 O 0.93496(8) 0.57511(16) 0.92371(5) 0.0406(3) Uani 1 1 d . . . . .
H1 H 0.9066 0.5112 0.9444 0.061 Uiso 1 1 d R U . . .
O2 O 0.86778(7) -0.05882(15) 0.87479(5) 0.0327(3) Uani 1 1 d . . . . .
H2 H 0.8890(5) -0.159(3) 0.8957(5) 0.049 Uiso 1 1 d R U . . .
O3 O 0.72403(7) 0.22448(15) 0.70500(5) 0.0322(3) Uani 1 1 d . . . . .
C1 C 0.81897(9) 0.3427(2) 0.80911(7) 0.0265(3) Uani 1 1 d . . . . .
C2 C 0.91121(9) 0.2718(2) 0.85204(7) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.91194(9) 0.1120(2) 0.90547(7) 0.0264(3) Uani 1 1 d . . . . .
H3 H 0.9747 0.0725 0.9227 0.032 Uiso 1 1 calc R U . . .
C4 C 0.88145(9) 0.1831(2) 0.96452(7) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.9263 0.2677 0.9945 0.032 Uiso 1 1 calc R U . . .
C5 C 0.82107(10) 0.0800(2) 1.00029(7) 0.0313(3) Uani 1 1 d . . . . .
C6 C 0.78871(10) 0.2572(2) 0.95787(7) 0.0297(3) Uani 1 1 d . . . . .
H6 H 0.7845 0.3815 0.9825 0.036 Uiso 1 1 calc R U . . .
C7 C 0.72466(10) 0.2430(2) 0.89119(7) 0.0312(3) Uani 1 1 d . . . . .
H7A H 0.6645 0.2668 0.8958 0.037 Uiso 1 1 calc R U . . .
H7B H 0.7266 0.1078 0.8737 0.037 Uiso 1 1 calc R U . . .
C8 C 0.74520(10) 0.3918(2) 0.84270(7) 0.0313(3) Uani 1 1 d . . . . .
H8A H 0.7601 0.5189 0.8661 0.038 Uiso 1 1 calc R U . . .
H8B H 0.6907 0.4134 0.8078 0.038 Uiso 1 1 calc R U . . .
C9 C 0.79299(10) 0.1690(2) 0.76057(7) 0.0278(3) Uani 1 1 d . . . . .
H9 H 0.7729 0.0556 0.7834 0.033 Uiso 1 1 calc R U . . .
C10 C 0.87698(11) 0.1110(3) 0.74187(7) 0.0363(4) Uani 1 1 d . . . . .
H10A H 0.8809 0.1792 0.7012 0.044 Uiso 1 1 calc R U . . .
H10B H 0.8787 -0.0334 0.7348 0.044 Uiso 1 1 calc R U . . .
C11 C 0.95257(10) 0.1749(3) 0.79976(7) 0.0349(4) Uani 1 1 d . . . . .
H11A H 0.9909 0.2707 0.7849 0.042 Uiso 1 1 calc R U . . .
H11B H 0.9883 0.0588 0.8187 0.042 Uiso 1 1 calc R U . . .
C12 C 0.82994(12) 0.5279(2) 0.76929(8) 0.0371(4) Uani 1 1 d . . . . .
H12A H 0.7748 0.5552 0.7367 0.056 Uiso 1 1 calc R U . . .
H12B H 0.8766 0.5050 0.7470 0.056 Uiso 1 1 calc R U . . .
H12C H 0.8454 0.6412 0.7989 0.056 Uiso 1 1 calc R U . . .
C13 C 0.97088(10) 0.4425(2) 0.88418(8) 0.0360(4) Uani 1 1 d . . . . .
H13A H 1.0256 0.3856 0.9119 0.043 Uiso 1 1 calc R U . . .
H13B H 0.9869 0.5202 0.8491 0.043 Uiso 1 1 calc R U . . .
C14 C 0.84500(11) 0.1186(3) 1.07357(7) 0.0429(4) Uani 1 1 d . . . . .
H14A H 0.8691 0.2523 1.0822 0.064 Uiso 1 1 calc R U . . .
H14B H 0.8889 0.0221 1.0957 0.064 Uiso 1 1 calc R U . . .
H14C H 0.7925 0.1066 1.0901 0.064 Uiso 1 1 calc R U . . .
C15 C 0.78195(12) -0.1227(3) 0.98338(8) 0.0426(4) Uani 1 1 d . . . . .
H15A H 0.7319 -0.1399 1.0026 0.064 Uiso 1 1 calc R U . . .
H15B H 0.8263 -0.2235 1.0009 0.064 Uiso 1 1 calc R U . . .
H15C H 0.7622 -0.1364 0.9356 0.064 Uiso 1 1 calc R U . . .
C16 C 0.69121(14) -0.1096(3) 0.61801(9) 0.0528(5) Uani 1 1 d . . . . .
H16A H 0.7207 -0.0391 0.5890 0.079 Uiso 1 1 calc R U . . .
H16B H 0.6433 -0.1894 0.5916 0.079 Uiso 1 1 calc R U . . .
H16C H 0.7334 -0.1959 0.6475 0.079 Uiso 1 1 calc R U . . .
C17 C 0.60038(17) -0.0601(4) 0.72831(11) 0.0670(6) Uani 1 1 d . . . . .
H17A H 0.6459 -0.1440 0.7556 0.100 Uiso 1 1 calc R U . . .
H17B H 0.5509 -0.1422 0.7055 0.100 Uiso 1 1 calc R U . . .
H17C H 0.5803 0.0362 0.7561 0.100 Uiso 1 1 calc R U . . .
C18 C 0.56086(11) 0.2340(3) 0.61232(9) 0.0467(4) Uani 1 1 d . . . . .
C19 C 0.54005(18) 0.4101(4) 0.65051(14) 0.0873(9) Uani 1 1 d . . . . .
H19A H 0.5930 0.4900 0.6663 0.131 Uiso 1 1 calc R U . . .
H19B H 0.5194 0.3632 0.6880 0.131 Uiso 1 1 calc R U . . .
H19C H 0.4943 0.4905 0.6219 0.131 Uiso 1 1 calc R U . . .
C20 C 0.47728(15) 0.1135(5) 0.58469(14) 0.0896(9) Uani 1 1 d . . . . .
H20A H 0.4501 0.0796 0.6203 0.134 Uiso 1 1 calc R U . . .
H20B H 0.4922 -0.0079 0.5646 0.134 Uiso 1 1 calc R U . . .
H20C H 0.4361 0.1918 0.5516 0.134 Uiso 1 1 calc R U . . .
C21 C 0.59516(15) 0.3111(4) 0.55545(11) 0.0689(6) Uani 1 1 d . . . . .
H21A H 0.5495 0.3900 0.5261 0.103 Uiso 1 1 calc R U . . .
H21B H 0.6109 0.1993 0.5312 0.103 Uiso 1 1 calc R U . . .
H21C H 0.6471 0.3934 0.5726 0.103 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 O3 1.6458(11) . ?
Si1 C17 1.856(2) . ?
Si1 C16 1.8635(19) . ?
Si1 C18 1.8866(19) . ?
O1 C13 1.435(2) . ?
O1 H1 0.8227 . ?
O2 C3 1.4185(17) . ?
O2 H2 0.83(2) . ?
O3 C9 1.4325(17) . ?
C1 C12 1.543(2) . ?
C1 C8 1.542(2) . ?
C1 C9 1.5444(19) . ?
C1 C2 1.5804(19) . ?
C2 C13 1.535(2) . ?
C2 C11 1.560(2) . ?
C2 C3 1.5600(19) . ?
C3 C4 1.521(2) . ?
C3 H3 1.0000 . ?
C4 C6 1.518(2) . ?
C4 C5 1.524(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.506(2) . ?
C5 C15 1.510(2) . ?
C5 C14 1.518(2) . ?
C6 C7 1.513(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.527(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.537(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.520(3) . ?
C18 C21 1.526(3) . ?
C18 C20 1.534(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Si1 C17 109.87(8) . . ?
O3 Si1 C16 109.86(8) . . ?
C17 Si1 C16 109.70(10) . . ?
O3 Si1 C18 105.21(7) . . ?
C17 Si1 C18 111.40(11) . . ?
C16 Si1 C18 110.71(9) . . ?
C13 O1 H1 109.0 . . ?
C3 O2 H2 109.7 . . ?
C9 O3 Si1 123.42(9) . . ?
C12 C1 C8 106.00(12) . . ?
C12 C1 C9 107.78(11) . . ?
C8 C1 C9 111.33(12) . . ?
C12 C1 C2 110.19(12) . . ?
C8 C1 C2 119.56(11) . . ?
C9 C1 C2 101.54(11) . . ?
C13 C2 C11 108.06(12) . . ?
C13 C2 C3 108.12(11) . . ?
C11 C2 C3 106.87(12) . . ?
C13 C2 C1 113.38(12) . . ?
C11 C2 C1 102.19(11) . . ?
C3 C2 C1 117.52(12) . . ?
O2 C3 C4 114.28(12) . . ?
O2 C3 C2 108.82(11) . . ?
C4 C3 C2 115.16(12) . . ?
O2 C3 H3 105.9 . . ?
C4 C3 H3 105.9 . . ?
C2 C3 H3 105.9 . . ?
C6 C4 C3 121.65(12) . . ?
C6 C4 C5 59.34(10) . . ?
C3 C4 C5 128.71(13) . . ?
C6 C4 H4 112.3 . . ?
C3 C4 H4 112.3 . . ?
C5 C4 H4 112.3 . . ?
C6 C5 C15 121.78(13) . . ?
C6 C5 C14 115.28(14) . . ?
C15 C5 C14 112.26(14) . . ?
C6 C5 C4 60.11(10) . . ?
C15 C5 C4 124.61(13) . . ?
C14 C5 C4 113.51(13) . . ?
C5 C6 C7 123.23(13) . . ?
C5 C6 C4 60.55(10) . . ?
C7 C6 C4 117.77(12) . . ?
C5 C6 H6 114.8 . . ?
C7 C6 H6 114.8 . . ?
C4 C6 H6 114.8 . . ?
C6 C7 C8 112.09(13) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C1 118.50(12) . . ?
C7 C8 H8A 107.7 . . ?
C1 C8 H8A 107.7 . . ?
C7 C8 H8B 107.7 . . ?
C1 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
O3 C9 C10 112.63(11) . . ?
O3 C9 C1 111.23(11) . . ?
C10 C9 C1 105.39(12) . . ?
O3 C9 H9 109.2 . . ?
C10 C9 H9 109.2 . . ?
C1 C9 H9 109.2 . . ?
C9 C10 C11 105.74(12) . . ?
C9 C10 H10A 110.6 . . ?
C11 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C10 C11 C2 107.53(12) . . ?
C10 C11 H11A 110.2 . . ?
C2 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
C2 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C2 116.09(13) . . ?
O1 C13 H13A 108.3 . . ?
C2 C13 H13A 108.3 . . ?
O1 C13 H13B 108.3 . . ?
C2 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C21 108.3(2) . . ?
C19 C18 C20 109.8(2) . . ?
C21 C18 C20 108.90(18) . . ?
C19 C18 Si1 110.19(14) . . ?
C21 C18 Si1 110.02(13) . . ?
C20 C18 Si1 109.56(16) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 Si1 O3 C9 47.17(15) . . . . ?
C16 Si1 O3 C9 -73.60(13) . . . . ?
C18 Si1 O3 C9 167.20(11) . . . . ?
C12 C1 C2 C13 41.16(16) . . . . ?
C8 C1 C2 C13 -81.95(16) . . . . ?
C9 C1 C2 C13 155.19(12) . . . . ?
C12 C1 C2 C11 -74.86(14) . . . . ?
C8 C1 C2 C11 162.03(13) . . . . ?
C9 C1 C2 C11 39.16(14) . . . . ?
C12 C1 C2 C3 168.56(12) . . . . ?
C8 C1 C2 C3 45.45(18) . . . . ?
C9 C1 C2 C3 -77.41(14) . . . . ?
C13 C2 C3 O2 -171.50(12) . . . . ?
C11 C2 C3 O2 -55.40(14) . . . . ?
C1 C2 C3 O2 58.61(16) . . . . ?
C13 C2 C3 C4 58.70(16) . . . . ?
C11 C2 C3 C4 174.80(12) . . . . ?
C1 C2 C3 C4 -71.19(16) . . . . ?
O2 C3 C4 C6 -64.11(17) . . . . ?
C2 C3 C4 C6 62.97(18) . . . . ?
O2 C3 C4 C5 10.0(2) . . . . ?
C2 C3 C4 C5 137.08(14) . . . . ?
C3 C4 C5 C6 -107.85(16) . . . . ?
C6 C4 C5 C15 109.97(17) . . . . ?
C3 C4 C5 C15 2.1(2) . . . . ?
C6 C4 C5 C14 -106.69(15) . . . . ?
C3 C4 C5 C14 145.46(15) . . . . ?
C15 C5 C6 C7 -8.8(2) . . . . ?
C14 C5 C6 C7 -150.62(14) . . . . ?
C4 C5 C6 C7 105.65(15) . . . . ?
C15 C5 C6 C4 -114.50(16) . . . . ?
C14 C5 C6 C4 103.73(15) . . . . ?
C3 C4 C6 C5 119.26(15) . . . . ?
C3 C4 C6 C7 4.8(2) . . . . ?
C5 C4 C6 C7 -114.45(15) . . . . ?
C5 C6 C7 C8 -143.07(14) . . . . ?
C4 C6 C7 C8 -71.69(17) . . . . ?
C6 C7 C8 C1 79.93(16) . . . . ?
C12 C1 C8 C7 -174.36(12) . . . . ?
C9 C1 C8 C7 68.70(16) . . . . ?
C2 C1 C8 C7 -49.24(18) . . . . ?
Si1 O3 C9 C10 96.88(14) . . . . ?
Si1 O3 C9 C1 -145.07(10) . . . . ?
C12 C1 C9 O3 -47.25(16) . . . . ?
C8 C1 C9 O3 68.61(15) . . . . ?
C2 C1 C9 O3 -163.06(11) . . . . ?
C12 C1 C9 C10 75.10(14) . . . . ?
C8 C1 C9 C10 -169.04(12) . . . . ?
C2 C1 C9 C10 -40.71(14) . . . . ?
O3 C9 C10 C11 147.28(13) . . . . ?
C1 C9 C10 C11 25.84(15) . . . . ?
C9 C10 C11 C2 -0.33(17) . . . . ?
C13 C2 C11 C10 -144.14(13) . . . . ?
C3 C2 C11 C10 99.71(14) . . . . ?
C1 C2 C11 C10 -24.31(15) . . . . ?
C11 C2 C13 O1 167.54(12) . . . . ?
C3 C2 C13 O1 -77.12(16) . . . . ?
C1 C2 C13 O1 55.04(17) . . . . ?
O3 Si1 C18 C19 -48.27(18) . . . . ?
C17 Si1 C18 C19 70.74(19) . . . . ?
C16 Si1 C18 C19 -166.90(17) . . . . ?
O3 Si1 C18 C21 71.14(15) . . . . ?
C17 Si1 C18 C21 -169.86(15) . . . . ?
C16 Si1 C18 C21 -47.50(17) . . . . ?
O3 Si1 C18 C20 -169.17(16) . . . . ?
C17 Si1 C18 C20 -50.16(18) . . . . ?
C16 Si1 C18 C20 72.19(18) . . . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.037



################################################################################
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compounds_13-14
_database_code_depnum_ccdc_archive 'CCDC 1540873'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         '0.85(C22 H26 N4 O6), 0.15(C22 H26 N4 O6)'
_chemical_formula_sum            'C22 H26 N4 O6'
_chemical_formula_weight         442.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7959(5)
_cell_length_b                   10.4916(6)
_cell_length_c                   13.2932(8)
_cell_angle_alpha                70.468(2)
_cell_angle_beta                 74.252(2)
_cell_angle_gamma                71.371(2)
_cell_volume                     1076.80(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            18060
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.128
_diffrn_reflns_theta_max         30.667
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6584
_reflns_number_gt                5516
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 The crystal contains two molecules of similar size and identical formulae
 statistically disordered. The refinement of the occupancy factors of the
 differing atoms gave a ratio of 85/15 which was then fixed.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0651P)²+0.3550P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6584
_refine_ls_number_parameters     343
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.045

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.78046(18) 0.73208(16) 0.82732(14) 0.0313(3) Uani 0.85 1 d . . P A 1
O2A O 0.56775(15) 0.90795(13) 0.86454(11) 0.0363(3) Uani 0.85 1 d . . P A 1
O1B O 0.8395(11) 0.6997(11) 0.8176(10) 0.041(2) Uani 0.15 1 d . U P B 2
O2B O 0.5914(9) 0.8568(9) 0.8403(8) 0.0461(18) Uani 0.15 1 d . U P B 2
O3 O 0.22069(14) 0.00094(11) 0.90093(7) 0.0420(2) Uani 1 1 d . . . . .
O4 O 0.23529(12) -0.19115(10) 0.86770(8) 0.0377(2) Uani 1 1 d . . . . .
O5 O 0.13810(16) -0.15622(12) 0.52233(9) 0.0500(3) Uani 1 1 d . . . . .
O6 O 0.23408(18) -0.01045(14) 0.37978(9) 0.0565(3) Uani 1 1 d . . . . .
N1 N 0.37664(12) 0.17516(10) 0.73946(8) 0.02719(19) Uani 1 1 d . . . . .
H1 H 0.3571 0.1440 0.8107 0.033 Uiso 1 1 calc R U . . .
N2 N 0.45347(12) 0.28275(10) 0.68896(8) 0.02615(19) Uani 1 1 d . . . . .
N3 N 0.24098(12) -0.06834(10) 0.83763(8) 0.02751(19) Uani 1 1 d . . . . .
N4 N 0.20309(14) -0.05920(12) 0.47841(9) 0.0354(2) Uani 1 1 d . . . . .
C1 C 0.50080(13) 0.32465(11) 0.75241(8) 0.0240(2) Uani 1 1 d . . . . .
C2 C 0.48561(15) 0.27012(12) 0.87426(9) 0.0292(2) Uani 1 1 d . . . . .
H2A H 0.5511 0.1723 0.8951 0.035 Uiso 1 1 calc R U . . .
H2B H 0.3703 0.2743 0.9100 0.035 Uiso 1 1 calc R U . . .
C3 C 0.55142(15) 0.36748(13) 0.90560(9) 0.0298(2) Uani 1 1 d . . . . .
H3A H 0.6121 0.3152 0.9659 0.036 Uiso 1 1 calc R U . . .
H3B H 0.4613 0.4436 0.9279 0.036 Uiso 1 1 calc R U . . .
C4 C 0.66519(14) 0.42606(12) 0.80224(9) 0.0267(2) Uani 1 1 d . . . . .
C5 C 0.58206(13) 0.44546(11) 0.70713(8) 0.0242(2) Uani 1 1 d . . . . .
C6 C 0.72380(15) 0.42613(13) 0.61203(9) 0.0302(2) Uani 1 1 d . . . . .
H6A H 0.7575 0.5143 0.5740 0.036 Uiso 1 1 calc R U . . .
H6B H 0.6927 0.3954 0.5593 0.036 Uiso 1 1 calc R U . . .
C7 C 0.86154(16) 0.31294(14) 0.66478(11) 0.0357(3) Uani 1 1 d . . . . .
H7A H 0.8503 0.2187 0.6735 0.043 Uiso 1 1 calc R U . . .
H7B H 0.9693 0.3223 0.6195 0.043 Uiso 1 1 calc R U . . .
C8 C 0.84502(15) 0.33531(13) 0.77489(10) 0.0331(2) Uani 1 1 d . . . . .
H8 H 0.8715 0.2458 0.8326 0.040 Uiso 1 1 calc R U . . .
C9 C 0.91676(14) 0.45228(13) 0.78106(10) 0.0309(2) Uani 1 1 d . . . . .
C10A C 0.74183(16) 0.53600(14) 0.80114(10) 0.0234(2) Uani 0.85 1 d . . P A 1
C10B C 0.7808(11) 0.5973(9) 0.8057(7) 0.0331(15) Uani 0.15 1 d . U P B 2
C11 C 0.45140(16) 0.58222(12) 0.68118(11) 0.0334(2) Uani 1 1 d . . . . .
H11A H 0.5027 0.6607 0.6519 0.050 Uiso 1 1 calc R U . . .
H11B H 0.3953 0.5807 0.6273 0.050 Uiso 1 1 calc R U . . .
H11C H 0.3723 0.5931 0.7476 0.050 Uiso 1 1 calc R U . . .
C12 C 1.02812(16) 0.51579(15) 0.67955(12) 0.0390(3) Uani 1 1 d . . . . .
H12A H 1.1378 0.4526 0.6751 0.059 Uiso 1 1 calc R U . . .
H12B H 0.9846 0.5297 0.6151 0.059 Uiso 1 1 calc R U . . .
H12C H 1.0336 0.6060 0.6832 0.059 Uiso 1 1 calc R U . . .
C13 C 0.99880(18) 0.40289(16) 0.88068(13) 0.0428(3) Uani 1 1 d . . . . .
H13A H 1.1116 0.3494 0.8629 0.064 Uiso 1 1 calc R U . . .
H13B H 0.9986 0.4842 0.9014 0.064 Uiso 1 1 calc R U . . .
H13C H 0.9385 0.3436 0.9412 0.064 Uiso 1 1 calc R U . . .
C14A C 0.67564(16) 0.65874(14) 0.82239(11) 0.0268(2) Uani 0.85 1 d . . P A 1
H14A H 0.5607 0.6960 0.8339 0.032 Uiso 0.85 1 calc R U P A 1
C15A C 0.7117(3) 0.8559(2) 0.8521(2) 0.0266(4) Uani 0.85 1 d . . P A 1
C16A C 0.8416(4) 0.9133(4) 0.8615(3) 0.0329(6) Uani 0.85 1 d . . P A 1
H16A H 0.8863 0.9663 0.7894 0.049 Uiso 0.85 1 calc R U P A 1
H16B H 0.9290 0.8360 0.8916 0.049 Uiso 0.85 1 calc R U P A 1
H16C H 0.7943 0.9749 0.9096 0.049 Uiso 0.85 1 calc R U P A 1
C14B C 0.6327(11) 0.5899(8) 0.8127(7) 0.0315(15) Uani 0.15 1 d . U P B 2
H14B H 0.5325 0.6586 0.8214 0.038 Uiso 0.15 1 calc R U P B 2
C15B C 0.7353(16) 0.8191(15) 0.8399(12) 0.024(2) Uani 0.15 1 d . U P B 2
C16B C 0.805(2) 0.905(3) 0.868(2) 0.038(4) Uani 0.15 1 d . U P B 2
H16D H 0.8380 0.9758 0.8031 0.056 Uiso 0.15 1 calc R U P B 2
H16E H 0.9006 0.8470 0.9010 0.056 Uiso 0.15 1 calc R U P B 2
H16F H 0.7240 0.9511 0.9207 0.056 Uiso 0.15 1 calc R U P B 2
C17 C 0.33209(13) 0.11864(11) 0.67783(8) 0.02339(19) Uani 1 1 d . . . . .
C18 C 0.26849(13) -0.00096(11) 0.72168(8) 0.02359(19) Uani 1 1 d . . . . .
C19 C 0.22715(13) -0.05923(11) 0.65650(9) 0.0253(2) Uani 1 1 d . . . . .
H19 H 0.1863 -0.1403 0.6874 0.030 Uiso 1 1 calc R U . . .
C20 C 0.24624(14) 0.00227(12) 0.54635(9) 0.0274(2) Uani 1 1 d . . . . .
C21 C 0.30698(15) 0.12093(13) 0.49945(9) 0.0309(2) Uani 1 1 d . . . . .
H21 H 0.3188 0.1623 0.4233 0.037 Uiso 1 1 calc R U . . .
C22 C 0.34941(15) 0.17732(12) 0.56387(9) 0.0290(2) Uani 1 1 d . . . . .
H22 H 0.3914 0.2577 0.5314 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C15A 1.356(2) . ?
O1A C14A 1.4023(19) . ?
O2A C15A 1.197(3) . ?
O1B C15B 1.365(14) . ?
O1B C10B 1.400(13) . ?
O2B C15B 1.199(15) . ?
O3 N3 1.2300(14) . ?
O4 N3 1.2282(13) . ?
O5 N4 1.2235(15) . ?
O6 N4 1.2254(15) . ?
N1 C17 1.3505(13) . ?
N1 N2 1.3842(13) . ?
N2 C1 1.2780(14) . ?
N3 C18 1.4534(14) . ?
N4 C20 1.4517(14) . ?
C1 C2 1.5101(15) . ?
C1 C5 1.5214(14) . ?
C2 C3 1.5314(16) . ?
C3 C4 1.5326(15) . ?
C4 C10A 1.5051(17) . ?
C4 C5 1.5522(15) . ?
C4 C8 1.5804(17) . ?
C4 C14B 1.697(7) . ?
C5 C11 1.5262(16) . ?
C5 C6 1.5323(16) . ?
C6 C7 1.5346(18) . ?
C7 C8 1.5203(18) . ?
C8 C9 1.5814(17) . ?
C9 C10A 1.5102(17) . ?
C9 C12 1.5240(18) . ?
C9 C13 1.5376(18) . ?
C9 C10B 1.677(9) . ?
C10A C14A 1.3236(18) . ?
C10B C14B 1.306(13) . ?
C15A C16A 1.500(3) . ?
C15B C16B 1.43(2) . ?
C17 C22 1.4171(15) . ?
C17 C18 1.4176(14) . ?
C18 C19 1.3871(14) . ?
C19 C20 1.3757(15) . ?
C20 C21 1.3961(16) . ?
C21 C22 1.3697(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15A O1A C14A 117.66(17) . . ?
C15B O1B C10B 121.1(9) . . ?
C17 N1 N2 119.08(9) . . ?
C1 N2 N1 115.26(9) . . ?
O4 N3 O3 123.13(10) . . ?
O4 N3 C18 118.23(10) . . ?
O3 N3 C18 118.62(9) . . ?
O5 N4 O6 123.67(11) . . ?
O5 N4 C20 118.54(11) . . ?
O6 N4 C20 117.78(11) . . ?
N2 C1 C2 128.19(10) . . ?
N2 C1 C5 120.28(9) . . ?
C2 C1 C5 111.52(9) . . ?
C1 C2 C3 104.43(9) . . ?
C2 C3 C4 104.52(9) . . ?
C10A C4 C3 118.95(9) . . ?
C10A C4 C5 120.40(9) . . ?
C3 C4 C5 105.31(9) . . ?
C10A C4 C8 86.56(9) . . ?
C3 C4 C8 119.09(10) . . ?
C5 C4 C8 105.57(9) . . ?
C3 C4 C14B 100.1(3) . . ?
C5 C4 C14B 105.0(3) . . ?
C8 C4 C14B 120.2(3) . . ?
C1 C5 C11 108.92(9) . . ?
C1 C5 C6 112.97(9) . . ?
C11 C5 C6 113.89(9) . . ?
C1 C5 C4 101.12(8) . . ?
C11 C5 C4 114.74(9) . . ?
C6 C5 C4 104.53(9) . . ?
C5 C6 C7 104.52(9) . . ?
C8 C7 C6 106.05(10) . . ?
C7 C8 C4 106.30(9) . . ?
C7 C8 C9 118.88(10) . . ?
C4 C8 C9 90.59(9) . . ?
C10A C9 C12 116.78(11) . . ?
C10A C9 C13 113.15(11) . . ?
C12 C9 C13 110.41(11) . . ?
C10A C9 C8 86.35(9) . . ?
C12 C9 C8 117.13(11) . . ?
C13 C9 C8 111.18(11) . . ?
C12 C9 C10B 100.5(3) . . ?
C13 C9 C10B 99.3(3) . . ?
C8 C9 C10B 116.5(3) . . ?
C14A C10A C4 131.05(12) . . ?
C14A C10A C9 132.24(12) . . ?
C4 C10A C9 96.37(10) . . ?
C14B C10B O1B 131.6(8) . . ?
C14B C10B C9 110.3(7) . . ?
O1B C10B C9 118.0(7) . . ?
C10A C14A O1A 117.95(13) . . ?
O2A C15A O1A 123.3(2) . . ?
O2A C15A C16A 126.8(2) . . ?
O1A C15A C16A 109.9(3) . . ?
C10B C14B C4 102.0(6) . . ?
O2B C15B O1B 126.5(11) . . ?
O2B C15B C16B 117.1(15) . . ?
O1B C15B C16B 116.3(15) . . ?
N1 C17 C22 120.43(10) . . ?
N1 C17 C18 122.88(10) . . ?
C22 C17 C18 116.69(9) . . ?
C19 C18 C17 121.89(10) . . ?
C19 C18 N3 116.24(9) . . ?
C17 C18 N3 121.86(9) . . ?
C20 C19 C18 118.92(10) . . ?
C19 C20 C21 121.31(10) . . ?
C19 C20 N4 118.74(10) . . ?
C21 C20 N4 119.94(10) . . ?
C22 C21 C20 119.63(10) . . ?
C21 C22 C17 121.54(10) . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound_14
_database_code_depnum_ccdc_archive 'CCDC 1540874'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 N4 O6'
_chemical_formula_sum            'C22 H26 N4 O6'
_chemical_formula_weight         442.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.8792(5)
_cell_length_b                   7.3830(3)
_cell_length_c                   18.5839(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.011(2)
_cell_angle_gamma                90
_cell_volume                     2173.37(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4298
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      66.42

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.830
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15654
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.795
_diffrn_reflns_theta_max         67.005
_diffrn_reflns_theta_full        67.005
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3806
_reflns_number_gt                3056
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+1.4311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3806
_refine_ls_number_parameters     303
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.67823(11) 0.1339(3) 0.07591(10) 0.0424(4) Uani 1 1 d . . . . .
N2 N 0.62782(11) 0.1838(3) 0.01499(10) 0.0432(5) Uani 1 1 d . . . . .
H2 H 0.6493(7) 0.2113(9) -0.0282(14) 0.065 Uiso 1 1 d R U . . .
N3 N 0.52083(14) 0.3215(3) -0.10713(10) 0.0497(5) Uani 1 1 d . . . . .
N4 N 0.28436(13) 0.3068(3) 0.04367(12) 0.0546(5) Uani 1 1 d . . . . .
O1 O 1.10973(9) 0.1828(2) 0.20630(8) 0.0427(4) Uani 1 1 d . . . . .
O2A O 1.10823(17) -0.1156(4) 0.2295(2) 0.0726(8) Uani 0.8 1 d . . P . .
O2B O 1.1342(7) -0.1066(13) 0.1809(6) 0.061(3) Uani 0.2 1 d D . P . .
O3 O 0.59622(12) 0.2977(3) -0.11657(9) 0.0664(5) Uani 1 1 d . . . . .
O4 O 0.47042(12) 0.3795(3) -0.15434(9) 0.0684(6) Uani 1 1 d . . . . .
O5 O 0.24351(12) 0.3918(3) -0.00337(11) 0.0765(6) Uani 1 1 d . . . . .
O6 O 0.25357(12) 0.2431(3) 0.09674(12) 0.0723(6) Uani 1 1 d . . . . .
C1 C 0.90341(13) 0.1451(3) 0.10232(11) 0.0359(5) Uani 1 1 d . . . . .
C2 C 0.81902(13) 0.0774(3) 0.13028(11) 0.0385(5) Uani 1 1 d . . . . .
C3 C 0.80524(14) 0.1992(4) 0.19426(12) 0.0459(6) Uani 1 1 d . . . . .
H3A H 0.7452 0.1995 0.2055 0.055 Uiso 1 1 calc R U . . .
H3B H 0.8404 0.1601 0.2376 0.055 Uiso 1 1 calc R U . . .
C4 C 0.83224(14) 0.3846(3) 0.16887(13) 0.0475(6) Uani 1 1 d . . . . .
H4A H 0.8488 0.4632 0.2106 0.057 Uiso 1 1 calc R U . . .
H4B H 0.7855 0.4436 0.1397 0.057 Uiso 1 1 calc R U . . .
C5 C 0.90802(13) 0.3522(3) 0.12300(12) 0.0380(5) Uani 1 1 d . . . . .
H5 H 0.9006 0.4265 0.0780 0.046 Uiso 1 1 calc R U . . .
C6 C 0.99828(13) 0.3846(3) 0.15912(11) 0.0375(5) Uani 1 1 d . . . . .
C7 C 1.03022(12) 0.1929(3) 0.16923(11) 0.0363(5) Uani 1 1 d . . . . .
C8 C 0.98191(13) 0.0662(3) 0.13924(12) 0.0389(5) Uani 1 1 d . . . . .
H8 H 0.9949 -0.0594 0.1407 0.047 Uiso 1 1 calc R U . . .
C9 C 0.89382(14) 0.1080(3) 0.02081(11) 0.0425(5) Uani 1 1 d . . . . .
H9A H 0.9324 0.1859 -0.0052 0.051 Uiso 1 1 calc R U . . .
H9B H 0.9061 -0.0204 0.0104 0.051 Uiso 1 1 calc R U . . .
C10 C 0.80168(14) 0.1533(3) -0.00132(11) 0.0438(5) Uani 1 1 d . . . . .
H10A H 0.7957 0.2809 -0.0172 0.053 Uiso 1 1 calc R U . . .
H10B H 0.7792 0.0732 -0.0409 0.053 Uiso 1 1 calc R U . . .
C11 C 0.75684(13) 0.1209(3) 0.06653(11) 0.0379(5) Uani 1 1 d . . . . .
C12 C 0.81677(15) -0.1249(3) 0.14808(14) 0.0523(6) Uani 1 1 d . . . . .
H12A H 0.8570 -0.1505 0.1892 0.079 Uiso 1 1 calc R U . . .
H12B H 0.8321 -0.1951 0.1062 0.079 Uiso 1 1 calc R U . . .
H12C H 0.7598 -0.1586 0.1603 0.079 Uiso 1 1 calc R U . . .
C13 C 1.00203(15) 0.4855(3) 0.23100(13) 0.0486(6) Uani 1 1 d . . . . .
H13A H 0.9688 0.4198 0.2650 0.073 Uiso 1 1 calc R U . . .
H13B H 0.9788 0.6076 0.2235 0.073 Uiso 1 1 calc R U . . .
H13C H 1.0608 0.4939 0.2506 0.073 Uiso 1 1 calc R U . . .
C14 C 1.05247(15) 0.4862(4) 0.10722(14) 0.0520(6) Uani 1 1 d . . . . .
H14A H 1.1108 0.4932 0.1281 0.078 Uiso 1 1 calc R U . . .
H14B H 1.0301 0.6088 0.0993 0.078 Uiso 1 1 calc R U . . .
H14C H 1.0512 0.4215 0.0611 0.078 Uiso 1 1 calc R U . . .
C15 C 1.14509(16) 0.0255(4) 0.22938(16) 0.0569(7) Uani 1 1 d D . . . .
C16 C 1.23032(14) 0.0578(4) 0.26591(16) 0.0577(7) Uani 1 1 d . . . . .
H16A H 1.2508 -0.0539 0.2897 0.087 Uiso 1 1 calc R U . . .
H16B H 1.2268 0.1538 0.3020 0.087 Uiso 1 1 calc R U . . .
H16C H 1.2694 0.0947 0.2301 0.087 Uiso 1 1 calc R U . . .
C17 C 0.54523(14) 0.2155(3) 0.02080(11) 0.0390(5) Uani 1 1 d . . . . .
C18 C 0.49028(14) 0.2797(3) -0.03715(12) 0.0397(5) Uani 1 1 d . . . . .
C19 C 0.40563(14) 0.3103(3) -0.02953(12) 0.0426(5) Uani 1 1 d . . . . .
H19 H 0.3701 0.3540 -0.0690 0.051 Uiso 1 1 calc R U . . .
C20 C 0.37366(14) 0.2768(3) 0.03567(13) 0.0437(5) Uani 1 1 d . . . . .
C21 C 0.42494(15) 0.2145(3) 0.09467(13) 0.0479(6) Uani 1 1 d . . . . .
H21 H 0.4017 0.1920 0.1396 0.057 Uiso 1 1 calc R U . . .
C22 C 0.50865(14) 0.1864(3) 0.08706(12) 0.0455(5) Uani 1 1 d . . . . .
H22 H 0.5435 0.1460 0.1275 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.276(3) . ?
N1 N2 1.390(2) . ?
N2 C17 1.344(3) . ?
N2 H2 0.92(3) . ?
N3 O4 1.223(2) . ?
N3 O3 1.235(3) . ?
N3 C18 1.453(3) . ?
N4 O5 1.225(3) . ?
N4 O6 1.225(3) . ?
N4 C20 1.453(3) . ?
O1 C15 1.347(3) . ?
O1 C7 1.397(2) . ?
O2A O2B 1.021(11) . ?
O2A C15 1.195(4) . ?
O2B C15 1.331(9) . ?
C1 C8 1.498(3) . ?
C1 C9 1.536(3) . ?
C1 C2 1.553(3) . ?
C1 C5 1.577(3) . ?
C2 C3 1.519(3) . ?
C2 C11 1.523(3) . ?
C2 C12 1.530(3) . ?
C3 C4 1.519(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.541(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.558(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.511(3) . ?
C6 C13 1.527(3) . ?
C6 C14 1.533(3) . ?
C7 C8 1.309(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.529(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.510(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.490(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C22 1.414(3) . ?
C17 C18 1.419(3) . ?
C18 C19 1.380(3) . ?
C19 C20 1.369(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.397(3) . ?
C21 C22 1.362(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 N2 114.95(19) . . ?
C17 N2 N1 119.37(19) . . ?
C17 N2 H2 117.2 . . ?
N1 N2 H2 122.9 . . ?
O4 N3 O3 122.7(2) . . ?
O4 N3 C18 118.3(2) . . ?
O3 N3 C18 118.99(19) . . ?
O5 N4 O6 123.4(2) . . ?
O5 N4 C20 118.5(2) . . ?
O6 N4 C20 118.1(2) . . ?
C15 O1 C7 123.01(18) . . ?
O2B O2A C15 73.4(6) . . ?
O2A O2B C15 59.3(6) . . ?
C8 C1 C9 113.84(18) . . ?
C8 C1 C2 115.54(18) . . ?
C9 C1 C2 104.13(16) . . ?
C8 C1 C5 104.04(16) . . ?
C9 C1 C5 114.37(18) . . ?
C2 C1 C5 104.90(17) . . ?
C3 C2 C11 111.30(18) . . ?
C3 C2 C12 113.7(2) . . ?
C11 C2 C12 110.51(18) . . ?
C3 C2 C1 104.24(17) . . ?
C11 C2 C1 101.50(16) . . ?
C12 C2 C1 114.85(19) . . ?
C4 C3 C2 103.37(18) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C3 C4 C5 106.28(19) . . ?
C3 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C4 C5 C6 117.92(18) . . ?
C4 C5 C1 105.09(17) . . ?
C6 C5 C1 106.22(16) . . ?
C4 C5 H5 109.1 . . ?
C6 C5 H5 109.1 . . ?
C1 C5 H5 109.1 . . ?
C7 C6 C13 110.86(18) . . ?
C7 C6 C14 109.77(18) . . ?
C13 C6 C14 108.81(19) . . ?
C7 C6 C5 101.57(16) . . ?
C13 C6 C5 115.48(18) . . ?
C14 C6 C5 110.12(17) . . ?
C8 C7 O1 130.9(2) . . ?
C8 C7 C6 115.77(19) . . ?
O1 C7 C6 113.26(17) . . ?
C7 C8 C1 111.2(2) . . ?
C7 C8 H8 124.4 . . ?
C1 C8 H8 124.4 . . ?
C10 C9 C1 104.67(17) . . ?
C10 C9 H9A 110.8 . . ?
C1 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
C1 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C11 C10 C9 103.83(17) . . ?
C11 C10 H10A 111.0 . . ?
C9 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
N1 C11 C10 128.69(19) . . ?
N1 C11 C2 119.80(19) . . ?
C10 C11 C2 111.42(17) . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2A C15 O2B 47.3(5) . . ?
O2A C15 O1 124.0(2) . . ?
O2B C15 O1 112.6(5) . . ?
O2A C15 C16 124.6(2) . . ?
O2B C15 C16 119.8(5) . . ?
O1 C15 C16 110.6(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C22 120.4(2) . . ?
N2 C17 C18 123.3(2) . . ?
C22 C17 C18 116.3(2) . . ?
C19 C18 C17 121.9(2) . . ?
C19 C18 N3 116.47(19) . . ?
C17 C18 N3 121.6(2) . . ?
C20 C19 C18 119.0(2) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 121.5(2) . . ?
C19 C20 N4 119.2(2) . . ?
C21 C20 N4 119.3(2) . . ?
C22 C21 C20 119.2(2) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C17 122.0(2) . . ?
C21 C22 H22 119.0 . . ?
C17 C22 H22 119.0 . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.039


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_7
_database_code_depnum_ccdc_archive 'CCDC 1540872'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         'C22 H26 N4 O6'
_chemical_formula_sum            'C22 H26 N4 O6'
_chemical_formula_weight         442.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.2372(12)
_cell_length_b                   19.7853(13)
_cell_length_c                   12.5770(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.983(3)
_cell_angle_gamma                90
_cell_volume                     4553.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    7312
_cell_measurement_theta_min      4.32
_cell_measurement_theta_max      50.13

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             1872
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            20905
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.319
_diffrn_reflns_theta_max         50.785
_diffrn_reflns_theta_full        50.785
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4753
_reflns_number_gt                3599
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1319P)²+2.5237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4753
_refine_ls_number_parameters     581
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.2182
_refine_ls_wR_factor_gt          0.2013
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.060

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30726(18) 0.36823(18) 0.8749(3) 0.0761(10) Uani 1 1 d . . . . .
O2 O 0.4005(2) 0.3083(3) 0.8503(3) 0.1000(13) Uani 1 1 d . . . . .
O3 O -0.1546(3) 0.6241(3) 0.5675(5) 0.157(2) Uani 1 1 d . . . . .
O4 O -0.1912(2) 0.5671(2) 0.4139(4) 0.1104(14) Uani 1 1 d . . . . .
O5 O -0.08956(18) 0.35441(18) 0.3865(3) 0.0792(10) Uani 1 1 d . . . . .
O6 O 0.0015(2) 0.3136(2) 0.5155(3) 0.0935(12) Uani 1 1 d . . . . .
O7 O -0.27637(17) 0.37387(17) 0.2276(2) 0.0695(9) Uani 1 1 d . . . . .
O8 O -0.2687(2) 0.3363(2) 0.0620(3) 0.0911(11) Uani 1 1 d . . . . .
O9 O -0.0530(2) 0.4544(2) 1.0392(3) 0.0884(11) Uani 1 1 d . . . . .
O10 O 0.0353(2) 0.3846(2) 1.0583(3) 0.0861(11) Uani 1 1 d . . . . .
O11 O 0.02140(18) 0.21792(17) 0.7775(3) 0.0735(9) Uani 1 1 d . . . . .
O12 O -0.07786(18) 0.20258(17) 0.6423(3) 0.0775(10) Uani 1 1 d . . . . .
N1 N 0.1086(2) 0.3889(2) 0.8064(3) 0.0605(10) Uani 1 1 d . . . . .
N2 N 0.06185(19) 0.38096(19) 0.6967(3) 0.0579(9) Uani 1 1 d . . . . .
H2N H 0.0669 0.3459 0.6566 0.069 Uiso 1 1 calc R U . . .
N3 N -0.1512(3) 0.5750(3) 0.5104(5) 0.0946(14) Uani 1 1 d . . . . .
N4 N -0.0436(2) 0.3594(2) 0.4788(3) 0.0672(11) Uani 1 1 d . . . . .
N5 N -0.23700(19) 0.33271(19) 0.5226(3) 0.0613(10) Uani 1 1 d . . . . .
N6 N -0.17274(19) 0.30128(19) 0.5833(3) 0.0597(10) Uani 1 1 d . . . . .
H6N H -0.1558 0.2665 0.5554 0.072 Uiso 1 1 calc R U . . .
N7 N -0.0240(3) 0.4082(3) 1.0060(3) 0.0726(11) Uani 1 1 d . . . . .
N8 N -0.0405(2) 0.2349(2) 0.7240(3) 0.0619(10) Uani 1 1 d . . . . .
C1 C 0.1597(2) 0.3447(2) 0.8348(3) 0.0579(11) Uani 1 1 d . . . . .
C2 C 0.1776(2) 0.2906(2) 0.7639(4) 0.0662(12) Uani 1 1 d . . . . .
H2A H 0.1854 0.3102 0.6961 0.079 Uiso 1 1 calc R U . . .
H2B H 0.1377 0.2569 0.7410 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2483(3) 0.2581(3) 0.8398(4) 0.0714(13) Uani 1 1 d . . . . .
H3A H 0.2375 0.2162 0.8747 0.086 Uiso 1 1 calc R U . . .
H3B H 0.2823 0.2474 0.7970 0.086 Uiso 1 1 calc R U . . .
C4 C 0.2804(2) 0.3127(2) 0.9284(4) 0.0668(13) Uani 1 1 d . . . . .
C5 C 0.2124(2) 0.3440(2) 0.9521(3) 0.0625(12) Uani 1 1 d . . . . .
C6 C 0.1833(3) 0.2951(3) 1.0233(4) 0.0834(15) Uani 1 1 d . . . . .
H6A H 0.1440 0.3170 1.0450 0.125 Uiso 1 1 calc R U . . .
H6B H 0.2230 0.2827 1.0906 0.125 Uiso 1 1 calc R U . . .
H6C H 0.1643 0.2543 0.9798 0.125 Uiso 1 1 calc R U . . .
C7 C 0.2242(3) 0.4146(3) 1.0041(4) 0.0797(15) Uani 1 1 d . . . . .
H7A H 0.1759 0.4335 1.0009 0.096 Uiso 1 1 calc R U . . .
H7B H 0.2448 0.4439 0.9574 0.096 Uiso 1 1 calc R U . . .
C8 C 0.2746(4) 0.4190(3) 1.1261(5) 0.108(2) Uani 1 1 d . . . . .
H8A H 0.2481 0.4014 1.1765 0.130 Uiso 1 1 calc R U . . .
H8B H 0.3179 0.3899 1.1348 0.130 Uiso 1 1 calc R U . . .
C9 C 0.2986(4) 0.4875(4) 1.1590(6) 0.129(3) Uani 1 1 d . . . . .
H9 H 0.2648 0.5154 1.1798 0.155 Uiso 1 1 calc R U . . .
C10 C 0.3616(5) 0.5160(4) 1.1637(7) 0.131(3) Uani 1 1 d . . . . .
C11 C 0.3755(6) 0.5879(5) 1.1956(8) 0.190(5) Uani 1 1 d . . . . .
H11A H 0.4246 0.6004 1.1947 0.285 Uiso 1 1 calc R U . . .
H11B H 0.3392 0.6162 1.1424 0.285 Uiso 1 1 calc R U . . .
H11C H 0.3719 0.5947 1.2709 0.285 Uiso 1 1 calc R U . . .
C12 C 0.4228(8) 0.4812(8) 1.1328(17) 0.313(11) Uani 1 1 d . . . . .
H12A H 0.4638 0.5126 1.1432 0.469 Uiso 1 1 calc R U . . .
H12B H 0.4392 0.4416 1.1808 0.469 Uiso 1 1 calc R U . . .
H12C H 0.4051 0.4669 1.0544 0.469 Uiso 1 1 calc R U . . .
C13 C 0.3367(3) 0.2879(3) 1.0267(4) 0.0795(15) Uani 1 1 d . . . . .
C14 C 0.3782(3) 0.2675(3) 1.1100(5) 0.0995(19) Uani 1 1 d . . . . .
H14 H 0.4118 0.2510 1.1773 0.119 Uiso 1 1 calc R U . . .
C15 C 0.3652(3) 0.3593(4) 0.8378(4) 0.0893(17) Uani 1 1 d . . . . .
C16 C 0.3768(4) 0.4236(5) 0.7817(6) 0.143(3) Uani 1 1 d . . . . .
H16A H 0.4163 0.4170 0.7487 0.214 Uiso 1 1 calc R U . . .
H16B H 0.3900 0.4601 0.8370 0.214 Uiso 1 1 calc R U . . .
H16C H 0.3317 0.4355 0.7228 0.214 Uiso 1 1 calc R U . . .
C17 C 0.0093(2) 0.4269(2) 0.6530(3) 0.0518(11) Uani 1 1 d . . . . .
C18 C 0.0041(2) 0.4857(2) 0.7115(4) 0.0571(11) Uani 1 1 d . . . . .
H18 H 0.0378 0.4929 0.7837 0.069 Uiso 1 1 calc R U . . .
C19 C -0.0484(3) 0.5330(2) 0.6668(4) 0.0658(13) Uani 1 1 d . . . . .
H19 H -0.0516 0.5724 0.7082 0.079 Uiso 1 1 calc R U . . .
C20 C -0.0972(2) 0.5234(2) 0.5604(4) 0.0645(12) Uani 1 1 d . . . . .
C21 C -0.0948(2) 0.4668(2) 0.5008(4) 0.0593(12) Uani 1 1 d . . . . .
H21 H -0.1289 0.4607 0.4286 0.071 Uiso 1 1 calc R U . . .
C22 C -0.0427(2) 0.4184(2) 0.5454(3) 0.0531(11) Uani 1 1 d . . . . .
C23 C -0.2664(2) 0.3076(2) 0.4247(4) 0.0596(12) Uani 1 1 d . . . . .
C24 C -0.2383(2) 0.2526(2) 0.3670(3) 0.0598(12) Uani 1 1 d . . . . .
H24A H -0.2393 0.2084 0.4035 0.072 Uiso 1 1 calc R U . . .
H24B H -0.1876 0.2622 0.3681 0.072 Uiso 1 1 calc R U . . .
C25 C -0.2905(2) 0.2525(3) 0.2466(3) 0.0671(13) Uani 1 1 d . . . . .
H25A H -0.2631 0.2471 0.1921 0.081 Uiso 1 1 calc R U . . .
H25B H -0.3266 0.2155 0.2355 0.081 Uiso 1 1 calc R U . . .
C26 C -0.3279(2) 0.3213(3) 0.2339(3) 0.0707(14) Uani 1 1 d . . . . .
C27 C -0.3392(2) 0.3348(3) 0.3498(4) 0.0688(13) Uani 1 1 d . . . . .
C28 C -0.4004(3) 0.2882(3) 0.3633(4) 0.0949(18) Uani 1 1 d . . . . .
H28A H -0.4028 0.2918 0.4398 0.142 Uiso 1 1 calc R U . . .
H28B H -0.3898 0.2413 0.3483 0.142 Uiso 1 1 calc R U . . .
H28C H -0.4473 0.3019 0.3104 0.142 Uiso 1 1 calc R U . . .
C29 C -0.3546(3) 0.4086(3) 0.3672(4) 0.0899(17) Uani 1 1 d . . . . .
H29A H -0.3105 0.4353 0.3703 0.108 Uiso 1 1 calc R U . . .
H29B H -0.3945 0.4243 0.3013 0.108 Uiso 1 1 calc R U . . .
C30 C -0.3758(5) 0.4240(4) 0.4713(6) 0.131(3) Uani 1 1 d . . . . .
H30A H -0.3314 0.4222 0.5371 0.158 Uiso 1 1 calc R U . . .
H30B H -0.4096 0.3884 0.4807 0.158 Uiso 1 1 calc R U . . .
C31 C -0.4120(7) 0.4925(6) 0.4686(9) 0.162(3) Uani 1 1 d . . . . .
H31 H -0.4628 0.4944 0.4294 0.195 Uiso 1 1 calc R U . . .
C32 C -0.3828(8) 0.5477(10) 0.5123(9) 0.223(8) Uani 1 1 d . . . . .
C33 C -0.4275(12) 0.6155(6) 0.5150(17) 0.339(14) Uani 1 1 d . . . . .
H33A H -0.3936 0.6512 0.5528 0.509 Uiso 1 1 calc R U . . .
H33B H -0.4536 0.6296 0.4384 0.509 Uiso 1 1 calc R U . . .
H33C H -0.4627 0.6071 0.5556 0.509 Uiso 1 1 calc R U . . .
C34 C -0.3006(8) 0.5483(11) 0.5702(13) 0.316(11) Uani 1 1 d . . . . .
H34A H -0.2853 0.5935 0.5999 0.474 Uiso 1 1 calc R U . . .
H34B H -0.2884 0.5155 0.6317 0.474 Uiso 1 1 calc R U . . .
H34C H -0.2752 0.5361 0.5164 0.474 Uiso 1 1 calc R U . . .
C35 C -0.3944(3) 0.3251(3) 0.1403(4) 0.0853(17) Uani 1 1 d . . . . .
C36 C -0.4510(4) 0.3235(4) 0.0680(5) 0.112(2) Uani 1 1 d . . . . .
H36 H -0.4964 0.3222 0.0099 0.135 Uiso 1 1 calc R U . . .
C37 C -0.2493(3) 0.3753(3) 0.1391(4) 0.0731(14) Uani 1 1 d . . . . .
C38 C -0.1938(3) 0.4284(3) 0.1533(5) 0.0907(16) Uani 1 1 d . . . . .
H38A H -0.1462 0.4110 0.1989 0.136 Uiso 1 1 calc R U . . .
H38B H -0.2072 0.4675 0.1906 0.136 Uiso 1 1 calc R U . . .
H38C H -0.1909 0.4421 0.0799 0.136 Uiso 1 1 calc R U . . .
C39 C -0.1362(2) 0.3251(2) 0.6869(3) 0.0525(11) Uani 1 1 d . . . . .
C40 C -0.1606(2) 0.3841(2) 0.7273(4) 0.0619(12) Uani 1 1 d . . . . .
H40 H -0.2034 0.4061 0.6819 0.074 Uiso 1 1 calc R U . . .
C41 C -0.1245(2) 0.4105(3) 0.8296(4) 0.0649(12) Uani 1 1 d . . . . .
H41 H -0.1423 0.4502 0.8550 0.078 Uiso 1 1 calc R U . . .
C42 C -0.0616(2) 0.3789(2) 0.8966(3) 0.0571(12) Uani 1 1 d . . . . .
C43 C -0.0347(2) 0.3222(2) 0.8616(3) 0.0572(12) Uani 1 1 d . . . . .
H43 H 0.0086 0.3013 0.9079 0.069 Uiso 1 1 calc R U . . .
C44 C -0.0716(2) 0.2954(2) 0.7574(3) 0.0522(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.346(7) . ?
O1 C4 1.464(6) . ?
O2 C15 1.199(7) . ?
O3 N3 1.221(6) . ?
O4 N3 1.231(6) . ?
O5 N4 1.228(5) . ?
O6 N4 1.241(5) . ?
O7 C37 1.367(6) . ?
O7 C26 1.456(6) . ?
O8 C37 1.204(6) . ?
O9 N7 1.209(5) . ?
O10 N7 1.221(5) . ?
O11 N8 1.220(4) . ?
O12 N8 1.234(4) . ?
N1 C1 1.282(6) . ?
N1 N2 1.403(5) . ?
N2 C17 1.343(5) . ?
N3 C20 1.454(7) . ?
N4 C22 1.434(6) . ?
N5 C23 1.285(5) . ?
N5 N6 1.384(5) . ?
N6 C39 1.360(5) . ?
N7 C42 1.463(6) . ?
N8 C44 1.457(6) . ?
C1 C2 1.500(6) . ?
C1 C5 1.510(6) . ?
C2 C3 1.541(6) . ?
C3 C4 1.538(7) . ?
C4 C13 1.452(7) . ?
C4 C5 1.559(7) . ?
C5 C7 1.529(7) . ?
C5 C6 1.537(7) . ?
C7 C8 1.544(7) . ?
C8 C9 1.451(10) . ?
C9 C10 1.320(11) . ?
C10 C11 1.480(11) . ?
C10 C12 1.515(14) . ?
C13 C14 1.176(7) . ?
C15 C16 1.505(10) . ?
C17 C18 1.398(6) . ?
C17 C22 1.423(6) . ?
C18 C19 1.364(6) . ?
C19 C20 1.390(6) . ?
C20 C21 1.356(6) . ?
C21 C22 1.374(6) . ?
C23 C24 1.499(6) . ?
C23 C27 1.525(6) . ?
C24 C25 1.537(6) . ?
C25 C26 1.526(7) . ?
C26 C35 1.448(7) . ?
C26 C27 1.562(6) . ?
C27 C29 1.520(7) . ?
C27 C28 1.544(7) . ?
C29 C30 1.517(8) . ?
C30 C31 1.520(12) . ?
C31 C32 1.273(15) . ?
C32 C34 1.523(19) . ?
C32 C33 1.60(2) . ?
C35 C36 1.184(7) . ?
C37 C38 1.470(8) . ?
C39 C40 1.411(6) . ?
C39 C44 1.412(6) . ?
C40 C41 1.363(6) . ?
C41 C42 1.392(6) . ?
C42 C43 1.364(6) . ?
C43 C44 1.389(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C4 120.5(5) . . ?
C37 O7 C26 119.7(4) . . ?
C1 N1 N2 113.7(4) . . ?
C17 N2 N1 119.9(4) . . ?
O3 N3 O4 123.3(5) . . ?
O3 N3 C20 117.8(5) . . ?
O4 N3 C20 118.9(5) . . ?
O5 N4 O6 120.7(4) . . ?
O5 N4 C22 119.5(4) . . ?
O6 N4 C22 119.8(4) . . ?
C23 N5 N6 114.2(4) . . ?
C39 N6 N5 118.9(4) . . ?
O9 N7 O10 123.9(4) . . ?
O9 N7 C42 118.5(5) . . ?
O10 N7 C42 117.6(5) . . ?
O11 N8 O12 122.4(4) . . ?
O11 N8 C44 118.9(4) . . ?
O12 N8 C44 118.7(4) . . ?
N1 C1 C2 128.2(4) . . ?
N1 C1 C5 120.3(4) . . ?
C2 C1 C5 111.5(4) . . ?
C1 C2 C3 104.5(4) . . ?
C4 C3 C2 103.7(4) . . ?
C13 C4 O1 111.6(4) . . ?
C13 C4 C3 114.0(4) . . ?
O1 C4 C3 108.3(4) . . ?
C13 C4 C5 114.8(4) . . ?
O1 C4 C5 103.0(4) . . ?
C3 C4 C5 104.2(4) . . ?
C1 C5 C7 112.1(4) . . ?
C1 C5 C6 108.7(4) . . ?
C7 C5 C6 111.0(4) . . ?
C1 C5 C4 99.6(3) . . ?
C7 C5 C4 115.0(4) . . ?
C6 C5 C4 109.8(4) . . ?
C5 C7 C8 116.1(4) . . ?
C9 C8 C7 112.5(6) . . ?
C10 C9 C8 128.2(7) . . ?
C9 C10 C11 120.6(9) . . ?
C9 C10 C12 124.7(8) . . ?
C11 C10 C12 114.6(10) . . ?
C14 C13 C4 175.0(6) . . ?
O2 C15 O1 124.1(6) . . ?
O2 C15 C16 127.8(6) . . ?
O1 C15 C16 108.0(7) . . ?
N2 C17 C18 121.0(4) . . ?
N2 C17 C22 122.0(4) . . ?
C18 C17 C22 117.0(4) . . ?
C19 C18 C17 121.3(4) . . ?
C18 C19 C20 119.8(4) . . ?
C21 C20 C19 121.1(4) . . ?
C21 C20 N3 118.9(5) . . ?
C19 C20 N3 120.0(5) . . ?
C20 C21 C22 119.7(4) . . ?
C21 C22 C17 121.1(4) . . ?
C21 C22 N4 117.0(4) . . ?
C17 C22 N4 121.9(4) . . ?
N5 C23 C24 128.8(4) . . ?
N5 C23 C27 120.3(4) . . ?
C24 C23 C27 110.9(4) . . ?
C23 C24 C25 104.7(4) . . ?
C26 C25 C24 104.2(4) . . ?
C35 C26 O7 111.3(4) . . ?
C35 C26 C25 113.6(4) . . ?
O7 C26 C25 109.6(4) . . ?
C35 C26 C27 114.0(4) . . ?
O7 C26 C27 102.9(4) . . ?
C25 C26 C27 104.6(4) . . ?
C29 C27 C23 115.6(4) . . ?
C29 C27 C28 111.7(4) . . ?
C23 C27 C28 107.9(4) . . ?
C29 C27 C26 112.8(4) . . ?
C23 C27 C26 98.6(3) . . ?
C28 C27 C26 109.4(4) . . ?
C30 C29 C27 115.7(5) . . ?
C29 C30 C31 113.8(6) . . ?
C32 C31 C30 128.1(14) . . ?
C31 C32 C34 117.9(19) . . ?
C31 C32 C33 124.0(15) . . ?
C34 C32 C33 118.0(14) . . ?
C36 C35 C26 174.1(7) . . ?
O8 C37 O7 122.8(5) . . ?
O8 C37 C38 126.0(5) . . ?
O7 C37 C38 111.1(5) . . ?
N6 C39 C40 120.0(4) . . ?
N6 C39 C44 123.5(4) . . ?
C40 C39 C44 116.4(4) . . ?
C41 C40 C39 121.8(4) . . ?
C40 C41 C42 119.6(4) . . ?
C43 C42 C41 121.3(4) . . ?
C43 C42 N7 120.2(4) . . ?
C41 C42 N7 118.5(5) . . ?
C42 C43 C44 119.0(4) . . ?
C43 C44 C39 121.8(4) . . ?
C43 C44 N8 116.8(4) . . ?
C39 C44 N8 121.4(4) . . ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound_21
_database_code_depnum_ccdc_archive 'CCDC 1540875'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H38 O3 Si'
_chemical_formula_sum            'C21 H38 O3 Si'
_chemical_formula_weight         366.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.0743(3)
_cell_length_b                   6.81490(10)
_cell_length_c                   21.2545(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.7090(10)
_cell_angle_gamma                90
_cell_volume                     2181.03(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      30.04

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29012
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.705
_diffrn_reflns_theta_max         30.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6416
_reflns_number_gt                5087
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+0.3985P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6416
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.27611(5) 0.05229(14) 0.18136(5) 0.0423(2) Uani 1 1 d . . . . .
H1 H 1.3168(9) -0.0219(16) 0.1972(4) 0.064 Uiso 1 1 d R U . . .
O2 O 1.10802(6) 0.33434(13) 0.24159(4) 0.0409(2) Uani 1 1 d . . . . .
O3 O 0.88871(5) 0.12692(11) 0.10251(3) 0.02664(16) Uani 1 1 d . . . . .
Si1 Si 0.80170(2) 0.27381(5) 0.10098(2) 0.02539(8) Uani 1 1 d . . . . .
C1 C 1.02843(6) -0.01645(15) 0.14395(4) 0.02147(19) Uani 1 1 d . . . . .
C2 C 1.12006(6) 0.07941(15) 0.16488(5) 0.02311(19) Uani 1 1 d . . . . .
C3 C 1.11891(6) 0.15990(17) 0.23231(5) 0.0266(2) Uani 1 1 d . . . . .
C4 C 1.13098(7) 0.01759(17) 0.28531(5) 0.0280(2) Uani 1 1 d . . . . .
H4 H 1.1907 -0.0466 0.2891 0.034 Uiso 1 1 calc R U . . .
C5 C 1.08360(8) 0.0335(2) 0.34634(5) 0.0357(3) Uani 1 1 d . . . . .
C6 C 1.05303(7) -0.11672(19) 0.29778(5) 0.0304(2) Uani 1 1 d . . . . .
H6 H 1.0700 -0.2550 0.3086 0.037 Uiso 1 1 calc R U . . .
C7 C 0.96999(7) -0.0972(2) 0.25579(5) 0.0334(3) Uani 1 1 d . . . . .
H7A H 0.9502 0.0413 0.2553 0.040 Uiso 1 1 calc R U . . .
H7B H 0.9222 -0.1778 0.2730 0.040 Uiso 1 1 calc R U . . .
C8 C 0.98585(7) -0.16319(17) 0.18846(5) 0.0282(2) Uani 1 1 d . . . . .
H8A H 0.9279 -0.2035 0.1687 0.034 Uiso 1 1 calc R U . . .
H8B H 1.0239 -0.2815 0.1910 0.034 Uiso 1 1 calc R U . . .
C9 C 0.97207(6) 0.16993(15) 0.13336(5) 0.0234(2) Uani 1 1 d . . . . .
H9 H 0.9613 0.2299 0.1753 0.028 Uiso 1 1 calc R U . . .
C10 C 1.03060(7) 0.30865(16) 0.09705(5) 0.0299(2) Uani 1 1 d . . . . .
H10A H 1.0183 0.4470 0.1078 0.036 Uiso 1 1 calc R U . . .
H10B H 1.0203 0.2906 0.0511 0.036 Uiso 1 1 calc R U . . .
C11 C 1.12665(7) 0.25265(16) 0.11784(6) 0.0297(2) Uani 1 1 d . . . . .
H11A H 1.1575 0.3655 0.1384 0.036 Uiso 1 1 calc R U . . .
H11B H 1.1601 0.2124 0.0810 0.036 Uiso 1 1 calc R U . . .
C12 C 1.03641(8) -0.12331(16) 0.08077(5) 0.0292(2) Uani 1 1 d . . . . .
H12A H 1.0709 -0.2441 0.0875 0.044 Uiso 1 1 calc R U . . .
H12B H 1.0665 -0.0380 0.0514 0.044 Uiso 1 1 calc R U . . .
H12C H 0.9770 -0.1560 0.0632 0.044 Uiso 1 1 calc R U . . .
C13 C 1.19932(7) -0.05861(17) 0.16198(5) 0.0288(2) Uani 1 1 d . . . . .
H13A H 1.1921 -0.1720 0.1904 0.035 Uiso 1 1 calc R U . . .
H13B H 1.2048 -0.1082 0.1186 0.035 Uiso 1 1 calc R U . . .
C14 C 1.13452(9) -0.0466(3) 0.40389(6) 0.0478(4) Uani 1 1 d . . . . .
H14A H 1.1753 0.0541 0.4211 0.072 Uiso 1 1 calc R U . . .
H14B H 1.1685 -0.1623 0.3920 0.072 Uiso 1 1 calc R U . . .
H14C H 1.0927 -0.0834 0.4358 0.072 Uiso 1 1 calc R U . . .
C15 C 1.02712(10) 0.2091(3) 0.36118(7) 0.0522(4) Uani 1 1 d . . . . .
H15A H 0.9958 0.2553 0.3225 0.078 Uiso 1 1 calc R U . . .
H15B H 1.0651 0.3143 0.3787 0.078 Uiso 1 1 calc R U . . .
H15C H 0.9838 0.1717 0.3920 0.078 Uiso 1 1 calc R U . . .
C16 C 0.79015(10) 0.3889(2) 0.17984(6) 0.0482(3) Uani 1 1 d . . . . .
H16A H 0.7857 0.2860 0.2118 0.072 Uiso 1 1 calc R U . . .
H16B H 0.7365 0.4702 0.1790 0.072 Uiso 1 1 calc R U . . .
H16C H 0.8422 0.4709 0.1902 0.072 Uiso 1 1 calc R U . . .
C17 C 0.81440(9) 0.4696(2) 0.04097(7) 0.0431(3) Uani 1 1 d . . . . .
H17A H 0.8627 0.5581 0.0549 0.065 Uiso 1 1 calc R U . . .
H17B H 0.7589 0.5441 0.0358 0.065 Uiso 1 1 calc R U . . .
H17C H 0.8283 0.4098 0.0007 0.065 Uiso 1 1 calc R U . . .
C18 C 0.70537(7) 0.10831(18) 0.07948(5) 0.0311(2) Uani 1 1 d . . . . .
C19 C 0.71943(9) 0.0121(2) 0.01557(7) 0.0473(3) Uani 1 1 d . . . . .
H19A H 0.6704 -0.0785 0.0053 0.071 Uiso 1 1 calc R U . . .
H19B H 0.7756 -0.0604 0.0175 0.071 Uiso 1 1 calc R U . . .
H19C H 0.7213 0.1137 -0.0170 0.071 Uiso 1 1 calc R U . . .
C20 C 0.61787(8) 0.2228(3) 0.07499(7) 0.0508(4) Uani 1 1 d . . . . .
H20A H 0.5688 0.1326 0.0645 0.076 Uiso 1 1 calc R U . . .
H20B H 0.6207 0.3231 0.0421 0.076 Uiso 1 1 calc R U . . .
H20C H 0.6082 0.2861 0.1155 0.076 Uiso 1 1 calc R U . . .
C21 C 0.70033(10) -0.0526(3) 0.12960(8) 0.0577(4) Uani 1 1 d . . . . .
H21A H 0.6855 0.0064 0.1698 0.087 Uiso 1 1 calc R U . . .
H21B H 0.7579 -0.1192 0.1346 0.087 Uiso 1 1 calc R U . . .
H21C H 0.6544 -0.1479 0.1165 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.4268(13) . ?
O1 H1 0.852(18) . ?
O2 C3 1.2174(14) . ?
O3 C9 1.4202(11) . ?
O3 Si1 1.6492(8) . ?
Si1 C17 1.8622(13) . ?
Si1 C16 1.8662(13) . ?
Si1 C18 1.8779(11) . ?
C1 C12 1.5373(14) . ?
C1 C8 1.5375(14) . ?
C1 C9 1.5387(14) . ?
C1 C2 1.5730(13) . ?
C2 C13 1.5241(14) . ?
C2 C3 1.5355(14) . ?
C2 C11 1.5532(14) . ?
C3 C4 1.4912(15) . ?
C4 C5 1.5140(16) . ?
C4 C6 1.5226(16) . ?
C4 H4 1.0000 . ?
C5 C6 1.5101(17) . ?
C5 C15 1.5108(18) . ?
C5 C14 1.5147(16) . ?
C6 C7 1.5083(14) . ?
C6 H6 1.0000 . ?
C7 C8 1.5298(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5271(15) . ?
C9 H9 1.0000 . ?
C10 C11 1.5418(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C20 1.5318(17) . ?
C18 C19 1.5322(18) . ?
C18 C21 1.5332(18) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 H1 111.0 . . ?
C9 O3 Si1 124.71(7) . . ?
O3 Si1 C17 109.94(5) . . ?
O3 Si1 C16 110.20(6) . . ?
C17 Si1 C16 109.33(7) . . ?
O3 Si1 C18 104.20(5) . . ?
C17 Si1 C18 111.54(6) . . ?
C16 Si1 C18 111.54(6) . . ?
C12 C1 C8 106.35(8) . . ?
C12 C1 C9 109.19(8) . . ?
C8 C1 C9 112.53(9) . . ?
C12 C1 C2 109.86(8) . . ?
C8 C1 C2 118.86(8) . . ?
C9 C1 C2 99.78(8) . . ?
C13 C2 C3 107.55(8) . . ?
C13 C2 C11 111.65(9) . . ?
C3 C2 C11 109.46(9) . . ?
C13 C2 C1 114.32(8) . . ?
C3 C2 C1 111.34(8) . . ?
C11 C2 C1 102.46(8) . . ?
O2 C3 C4 121.68(10) . . ?
O2 C3 C2 120.51(10) . . ?
C4 C3 C2 117.81(9) . . ?
C3 C4 C5 123.72(10) . . ?
C3 C4 C6 117.05(8) . . ?
C5 C4 C6 59.64(8) . . ?
C3 C4 H4 115.0 . . ?
C5 C4 H4 115.0 . . ?
C6 C4 H4 115.0 . . ?
C6 C5 C15 121.53(10) . . ?
C6 C5 C4 60.46(7) . . ?
C15 C5 C4 121.93(12) . . ?
C6 C5 C14 115.75(12) . . ?
C15 C5 C14 112.70(11) . . ?
C4 C5 C14 115.12(10) . . ?
C7 C6 C5 124.23(10) . . ?
C7 C6 C4 118.02(9) . . ?
C5 C6 C4 59.90(8) . . ?
C7 C6 H6 114.5 . . ?
C5 C6 H6 114.5 . . ?
C4 C6 H6 114.5 . . ?
C6 C7 C8 111.45(9) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C1 118.20(9) . . ?
C7 C8 H8A 107.8 . . ?
C1 C8 H8A 107.8 . . ?
C7 C8 H8B 107.8 . . ?
C1 C8 H8B 107.8 . . ?
H8A C8 H8B 107.1 . . ?
O3 C9 C10 114.46(8) . . ?
O3 C9 C1 111.56(8) . . ?
C10 C9 C1 104.87(8) . . ?
O3 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
C1 C9 H9 108.6 . . ?
C9 C10 C11 105.02(8) . . ?
C9 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C10 C11 C2 106.55(8) . . ?
C10 C11 H11A 110.4 . . ?
C2 C11 H11A 110.4 . . ?
C10 C11 H11B 110.4 . . ?
C2 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C2 106.76(9) . . ?
O1 C13 H13A 110.4 . . ?
C2 C13 H13A 110.4 . . ?
O1 C13 H13B 110.4 . . ?
C2 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si1 C16 H16A 109.5 . . ?
Si1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
Si1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Si1 C17 H17A 109.5 . . ?
Si1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Si1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C18 C19 108.52(10) . . ?
C20 C18 C21 109.69(11) . . ?
C19 C18 C21 108.87(12) . . ?
C20 C18 Si1 111.27(9) . . ?
C19 C18 Si1 109.57(8) . . ?
C21 C18 Si1 108.89(8) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.041


